N,N-diethyl-1,2-dihydrocyclopenta[b]chromen-6-amine | 203525-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N,N-diethyl-1,2-dihydrocyclopenta[b]chromen-6-amine
• CAS: 203525-19-3
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: ITAHFMZTCLXFOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-1,2-dihydrocyclopenta[b]chromen-6-amine 在 高氯酸 作用下， 以 乙醚 为溶剂， 以40%的产率得到
  参考文献：
  名称：

  On the Formation and Reactivity of 2-Alkylidene-benzopyrans and their 2-amino-5,6-benzo-2H-pyran precursors

  摘要：

  A series of 2-amino-substituted 5,6-benzo-2H-pyrans 14, 2-alkylidene-5,6-benzo-2H-pyrans 15, and their dimers 17 are obtained, depending on the condition used, by the reaction of 2-hydroxy-benzaldehydes I with enamines 9 derived of (cyclo)aliphatic ketones. Compounds 14, 15, and 17 can be transformed into 2-alkyl-benzopyrylium salts 16 or 2-[1-(2-hydroxyphenyl)-alken-2-yl]-benzopyrylium salts 23 by treatment with mineral acids. With aromatic aldehydes or the Vilsmeier reagent the compounds 14, 15, or 17 are transformed into deeply colored 2-(aryl-alkenyl)-benzopyrylium perchlorates 25 or 2-(2-dialkylamino)-alkenyl-benzopyrylium salts 26, respectively.

  DOI：

  10.1002/prac.19983400106
• 作为产物：
  描述：

  1-(1-吡咯烷)环戊烯 在 乙酸酐 作用下， 以 甲苯 、 乙腈 为溶剂， 生成 N,N-diethyl-1,2-dihydrocyclopenta[b]chromen-6-amine
  参考文献：
  名称：

  On the Formation and Reactivity of 2-Alkylidene-benzopyrans and their 2-amino-5,6-benzo-2H-pyran precursors

  摘要：

  A series of 2-amino-substituted 5,6-benzo-2H-pyrans 14, 2-alkylidene-5,6-benzo-2H-pyrans 15, and their dimers 17 are obtained, depending on the condition used, by the reaction of 2-hydroxy-benzaldehydes I with enamines 9 derived of (cyclo)aliphatic ketones. Compounds 14, 15, and 17 can be transformed into 2-alkyl-benzopyrylium salts 16 or 2-[1-(2-hydroxyphenyl)-alken-2-yl]-benzopyrylium salts 23 by treatment with mineral acids. With aromatic aldehydes or the Vilsmeier reagent the compounds 14, 15, or 17 are transformed into deeply colored 2-(aryl-alkenyl)-benzopyrylium perchlorates 25 or 2-(2-dialkylamino)-alkenyl-benzopyrylium salts 26, respectively.

  DOI：

  10.1002/prac.19983400106

文献信息

• 3,1?-Bridged 2-[2?-(4?-dialkylaminophenyl)ethenyl] pyrylium and 1-Benzopyrylium Dyes - Synthesis and Vis/NIR Absorption/Emission Behaviour
  作者：Peter Czerney、Ulrich-W. Grummt、Wolfgang G�nther

  DOI：10.1002/prac.19983400304

  日期：——

  A series of new 3,1'-bridged 2-[2'-(4 "-dialkylaminophenyl)ethenyl]-4,6-diarylpyrylium perchlorates (3), 2-[2'-(4 "-dialkylaminophenyl)ethenyl]-7-diethylamino-1-benzopyrylium perchlorates 5-8, 2-[4'-(4 "-dialkylaminophenyl)butadien-1',3'-yl]-, and 2-[2'-(7 "-diethylaminocoumar-3 "-yl)ethenyl]-7-diethylamino-1-benzopyrylium perchlorates 10-12 were synthesized and characterized by means of elemental analysis, m.p., Vis/NIR, and H-1 NMR spectra. Semiempirical MO calculations were performed to elucidate the essential features of the chromophores. The size of the bridging ring strongly affects the geometry of the chromophores which, in turn, determines the extent of charge transfer of the longest wavelength electronic transition. Increasing deviation from planarity causes the polymethine-like chromophore to become more polyene-like.